We bring you to two irresistible Italian realms in full WT style, with stunning hikes each day and expert Trip Leaders who bring this celebrated land to life. Our hikes cross Tuscany's harmonious landscape, discovering terraced vineyards, tiny hamlets, and classic hill towns on our way from San Quirico d'Orcia, once a stop for pilgrims on the Via Francigena, to Volterra, with its Etruscan origins. After a walk on Lucca's historic walls, we head to Cinque Terre, where five ancient villages nestle on cliffs and along deep coves on the Ligurian Coast. We connect these seaside villages with breathtaking hikes, sample Liguria's fresh-caught seafood, and ferry to Palmaria Island for a final hike with spectacular Cinque Terre panoramas.
Arrive: Florence, Italy
Depart: Pisa, Italy
Pricing below is per person and based on double occupancy. The earlier you book, the more choice you’ll have. WT also has the most generous cancellation and transfer policies in the industry, we make it easy if you change your mind. Have a small group of your own? Take over an existing date or choose your own. You’ll have your own private guide–and the adventure–all to yourselves!
$600 due at time of reservation
90 days prior to departure: Balance
Up to 91 days prior to departure: No Charge!
61-90 days prior to departure: 25% of trip cost
46-60 days prior to departure: 50% of trip cost
45 days or less: 100% of trip cost
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
San Quirico d'Orcia, Italy
Days 1-2 (2 nights)
This small hotel, a beautifully restored 15th century building with old world charm, is a nice surprise in the heart of the unspoiled village of San Quirico. Guest rooms are decorated in Tuscan style, with wooden beamed ceilings, antiques, and terracotta floors. Relax at the end of the day...
San Gimignano, Italy
Days 3-4 (2 nights)
Set in a beautiful park-like location just outside San Gimignano, this former 16th century convent for Capuchin friars and, later, a private family summer residence, is a wonderful retreat that retains an air of quiet elegance. Each of the 20 guest rooms rooms are individually decorated in Tuscan country style, but offer...
Days 5-6 (2 nights)
We love this gem of a hotel, set in the center of town and convenient to all the key sights, including access to walks and bike rides atop the town ramparts. (You can borrow one of the hotel's bikes for a leisurely ramble.) As befitting its medieval origins, the main...
Days 7-9 (3 nights)
Perched on a hillside above the sea, this 43-room hotel has “romance” written all over it. Several terraces cascade down the hill, each equipped with lounge chairs for gazing at the incredible scenery. The secluded infinity pool overlooks a small sheltered bay and there is a small wellness center. Guestrooms...
Giuseppe ArutaView Profile
Teresa BaldiView Profile
Lisa HaldermanView Profile
Isabelle JohnsonView Profile
JoAnn LantzView Profile
Vicky SotrifferView Profile
Amy BarnesView Profile
Irene De BenedictisView Profile
This trip is rated Level 3, Moderate, according to our trip grading system. While we do not see major elevation gain or loss, you will need to be comfortable hiking up to 6 miles a day and being on your feet for 4-5 hours a day. Trail conditions, weather, and the group's level of fitness can affect hiking times and pacing.Average Hiking Day
"I was a tour guide myself in my younger years; thus, I feel qualified to address all the fine qualities of this experience. Wonderful human touches brought so much life to this trip: the cozy restaurants, charming hotels, the farms and vineyards, and above all, our three guides—lovely human beings, and so professional. Superb!"
Twin Lakes, CO
"This was a great itinerary that was well organized and well executed. We had great food and wine at every destination and very well-informed trip leaders."
Highland Park, IL
"I LOVED THIS TRIP. As I look back, I have nothing but happy memories of each and every day. Our group was amazing as far as getting along and making new friendships. I have a new love for Italy and the countryside, as well as the traditions and language, all because of this trip and these guides and all the careful prep put into the whole thing. Cannot thank you enough."
"Outstanding trip, thank you! I absolutely loved the hiking and felt like we were seeing off-the-beaten-tourist-track places. Great guides, really good food, and the Italian Riviera was spectacular—especially the last day hiking out of Portofino to the cove with the big seafood lunch on the beach. What a way to end the trip! It was fabulous in every way. This was one of my favorite trips ever, and I've traveled extensively throughout the world. I can't wait to do another one with you."
"I was very impressed with this trip. Our guides were wonderful, and I loved seeing some of the out-of-the-way villages we hiked through. It was great to be off the beaten path."
"Our trip was fabulous on every front—we felt very well taken care of."
Twin Lakes, CO
"This was a well-designed trip which we very much enjoyed. Our Trip Leader JoAnn was well informed, organized and very engaging throughout our trip. We learned a great deal on our hikes and so enjoyed the museum tours and the guides she chose to lead them. We have always spoken highly of WT to our friends and family."
"Excellent lodging at hotels that we would return on our own. Can't say enough about the talents of our leaders in putting together the picnic lunches. This was our first trip of this kind, and I expect we'll be back. Sicily? Dolomites? All in all, it was a great value for the money, and I so appreciated the mix of hiking and in-town visits. "
Jamaica Plain, MA
"I enjoy reliving the beauty of the countryside, the plethora of information received, the charm of the medieval cities, the delicious picnics, and the company of interesting, intelligent, cheerful people—both fellow tour members and the wonderful trip leaders."
"It was an overall wonderful experience—we didn’t have to think about anything (other than what to order for dinner)."
Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
Submit the form below to download itinerary
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult—see descriptions below for explanations of each number. A plus (+) sign means the trip is a bit more strenuous than other trips of that level. The detailed explanation of each trip—below the bar with the number rating—is perhaps more important, specifying activities, altitudes, hiking, and travel conditions. The Detailed Itinerary, available by download or mail, gives further information. Our Area Managers can also answer questions and guide you to the trip that best suits your interests.
Level 1 – Easiest
Non-camping journeys, optional walks, little elevation gain or loss.
Level 3 – Moderate
Half- to full-day hikes (3-6 hours) over rolling countryside on most days, occasional steep trails. Many of our hotel-based walking tours are in this category, as are our snorkeling adventures.
Level 5 – Strenuous
Full-day hikes (4-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Trips with hiking at average altitudes of 10,000 to 12,000 feet are in this category.